1,3,8-Trihydroxy-6-{2-[2-(2-hydroxyethoxy)-ethoxy]-ethoxymethyl}-10H-anthracene-9-one | 171782-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,8-Trihydroxy-6-{2-[2-(2-hydroxyethoxy)-ethoxy]-ethoxymethyl}-10H-anthracene-9-one
• 英文别名: 1,3,8-trihydroxy-6-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl]-10H-anthracen-9-one
• CAS: 171782-03-9
• 化学式: C₂₁H₂₄O₈
• 分子量: 404.417
• InChiKey: PXOPGRLVVSLHOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,8-Trihydroxy-6-{2-[2-(2-hydroxyethoxy)-ethoxy]-ethoxymethyl}-10H-anthracene-9-one 在 吡啶-N-氧化物 作用下， 生成 hypericin PEG-3
  参考文献：
  名称：

  Synthesis and Properties of Ionophore Conjugated Hypericin Derivatives

  摘要：

  Two types of derivatives substituted with ionophoric residues at the omega,omega'-methyl groups of hypericin were synthesized. On the one hand, an open chain triethylene glycol derivative did not form stable complexes with alkali metal ions. Embedded as its detergent salt in lipid bilayer membranes it did not provide specific proton, sodium, or potassium channels. On the other hand, crown-4 and crown-5 hypericin derivatives were able to complex sodium and potassium ions, with the crown-5 compound forming a stable potassium crown complex. In such systems, the hypericinate ion is intramolecularly compensated by the complexed cation, thereby forming an extremal structure within the series of hypericinates.

  DOI：

  10.1007/pl00010159
• 作为产物：
  描述：

  1,3,8-Trihydroxy-6-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxymethyl}-anthraquinone 在 盐酸 、 tin(ll) chloride 作用下， 以78%的产率得到1,3,8-Trihydroxy-6-{2-[2-(2-hydroxyethoxy)-ethoxy]-ethoxymethyl}-10H-anthracene-9-one
  参考文献：
  名称：

  Synthesis and Properties of Ionophore Conjugated Hypericin Derivatives

  摘要：

  Two types of derivatives substituted with ionophoric residues at the omega,omega'-methyl groups of hypericin were synthesized. On the one hand, an open chain triethylene glycol derivative did not form stable complexes with alkali metal ions. Embedded as its detergent salt in lipid bilayer membranes it did not provide specific proton, sodium, or potassium channels. On the other hand, crown-4 and crown-5 hypericin derivatives were able to complex sodium and potassium ions, with the crown-5 compound forming a stable potassium crown complex. In such systems, the hypericinate ion is intramolecularly compensated by the complexed cation, thereby forming an extremal structure within the series of hypericinates.

  DOI：

  10.1007/pl00010159

文献信息

• On the synthesis of ?-appended hypericin derivatives
  作者：H. Falk、A. F. Vaisburg、A. M. Amer

  DOI：10.1007/bf00811019

  日期：——

  A method for the preparation of bis-omega-appended hypericin derivatives bearing n-octyl n-hexadecyl, and 2-(2-(2-hydroxyethoxy)-ethoxy)-ethoxymethyl substituents was developed. The key step - the synthesis of appropriately omega-substituted emodin derivatives - was achieved by solvolyzing 3-bromomethyl-1,6,8-triacetyloxy-anthracene-9,10-dione (omega-bromo triacetylemodin) in an appropriate alcohol in the presence of silver perchlorate. The corresponding bis-omega-substituted hypericins were then prepared conventionally by dimerizing the omega-substituted emodin anthrones. The latter were prepared by reduction of the omega-appended emodins.
• Synthesis and Properties of Ionophore Conjugated Hypericin Derivatives
  作者：Robert Altmann、Heinz Falk、Hermann J. Gruber

  DOI：10.1007/pl00010159

  日期：1998.3

  Two types of derivatives substituted with ionophoric residues at the omega,omega'-methyl groups of hypericin were synthesized. On the one hand, an open chain triethylene glycol derivative did not form stable complexes with alkali metal ions. Embedded as its detergent salt in lipid bilayer membranes it did not provide specific proton, sodium, or potassium channels. On the other hand, crown-4 and crown-5 hypericin derivatives were able to complex sodium and potassium ions, with the crown-5 compound forming a stable potassium crown complex. In such systems, the hypericinate ion is intramolecularly compensated by the complexed cation, thereby forming an extremal structure within the series of hypericinates.